The 4 Most Depressing Happy Endings In Hollywood Movies


When it comes to Hollywood movies it has to be said we all prefer a happy ending over a miserable and sad ending. Hollywood movie studios are well aware of this fact and as a result you will find very few movies that actually do not have a happy ending.

That said there are plenty of movies out there which, on the surface, may seem like they have a happy ending but if you look just a little closer those happy endings we all know and love are actually the most depressing endings you could imagine.

Pretty Woman

Pretty Woman is the romantic comedy movie 1990’s that made it cool and glamorous to be a prostitute working on Sunset Boulevard.

The typical attire for a streetwalker in Hollywood - apparently!
The typical attire for a streetwalker in Hollywood – apparently!

Julia Roberts plays the part of a hooker who is asked for directions by millionaire businessman, Richard Gere. He subsequently hires her to be his pretend girlfriend for a week accompanying him to various business dinners and functions.

The Happy Ending

Despite some unfortunate twists and turns Richard Gere and Julia Roberts get to the end of their week together and decide that they have fallen helplessly in love and are going to spend the rest of their lives together living happily ever after.

The Reality

First of all let me point out that anyone who has ever wandered down the not so nice part of Sunset Boulevard will tell you the hookers who patrol the area look nothing like Julia Roberts. In fact most of the girls working that area you will probably find are in that line of work because they have a rather expensive drug habit. Let u make no mistake the life of a Sunset Boulevard streetwalker is anything but glamorous. The girls are cheap and so are the services that they offer. This all makes the chances of our millionaire lead character picking up a girl that is even the slightest bit classy very remote indeed.

A more realistic happy ending in Hollywood
A more realistic happy ending in Hollywood

Let us just suppose for one second that a millionaire business man and a cheap five dollar hooker manage to hit it off and actually fall in love. Are we really expected to believe that such a relationship would last? For the unlikely pair to have any chance the hooker in question is going to need to turn her back on all of her friends which is a huge ask. It is highly unlikely that Richard Gere, regardless of how bad his career may have turned out, will want to come home from a long day at the office to find his house full of Julia Roberts’s streetwalking friends.

Let us not forget that the majority of hookers, especially those who work Sunset Boulevard, actually have pimps. How long before the pimps show up and start asking for a few free bucks?

There is just way to many things that Julia Roberts character is going to have to change for this relationship to ever work. The simple reality is that it is only a matter of time before she turns back to drugs, her old friends and her former pimp shows up. Oh, and Richard Gere finds someone with a little more class to fool around with behind her back.

All of this happens well before you even think about he consequences for a guy of Richard Gere’s social status. Hands up who remembers Hugh Grant and Divine Brown.


There are probably only a handful of people on the planet who did not get a chance to see the James Cameron film, Titanic. The movie tells the story of the ill-fated ocean liner and two born to lose lovers by the name of Rose and Jack. Rose is from a wealthy background and engaged to be married to a millionaire while Jack is third class passenger who does not have two cents to rub together.

You cannot help but feel that someone should tell them all the hassle they put themselves through probably isn’t worth it because the ship is going to hit an iceberg and sink.

The Happy Ending

Okay, so it is pretty hard to find anything happy about a movie in which 1500 people die in a shipwreck and one of the two main characters freeze to death in the water. That said the ending is supposed to be a little bit uplifting.

Not a dry eye in the house
Not a dry eye in the house

We see the camera move past photos showing us that Rose has led a very full life filled with adventure, love and laughter. The elderly Rose then quietly dies in her sleep and we see her reunited in the afterlife with all those people who died on in the Titanic disaster including her lost lover Jack.

The Reality

While it is all very sweet and romantic that after a lifetime Rose dies and then gets to spend eternity in the afterlife with Jack there is a problem or two with this situation.

We know that Rose has obviously had her own children and therefore this means she was probably married to someone. This leads you to ask what on earth happens to her husband in this afterlife. If everyone she has ever known is waiting for in heaven it is highly unlikely that any of these people are going to be okay with her turning up and then running off with Jack who she has never told anyone about.

You have to feel a little sorry for the guy who was Rose’s husband. Unless she is thinking that there is going to be some sort of afterlife threesome going on.

Jerry Maguire

Tom Cruise plays Jerry Maguire a high profile sports agent who has a major burnout and stakes his entire career on Rod Tidwell, a moody, hot headed football player who no one wants to hire.

The Happy Ending

After fighting off competition from other hungry sports agents and worrying about potential injuries to his only client everything falls nicely into place for Jerry Maguire. His only client has the most amazing season ever and is offered a huge contract to finish of his football career in style. As a result it also looks like other athletes have noticed the close personal attention Jerry Maguire offers to his clients and want a piece of that action.

Even the kid out acts Tom Cruise
Even the kid out acts Tom Cruise

As the movie ends we also see that Jerry Maguire’s love life has also sorted itself out and he is living happily ever after with his wife and her young son. As the final scene closes we see his step son throw a ball and hear Jerry Maguire comment that the kid has a natural talent and that could lead to something.

The Reality

The problem with Jerry Maguire is that he was and is a high profile lawyer and that is going to be something which is very hard to change in the long term. Sure, Jerry Maguire has a special relationship with his one and only client but that can very quickly change when more athletes need representation. We also know that much of Jerry Maguire’s final success is because Rod Tidewell, his only client, has ridden his ass like Zorro to get there.

Just like Zorro!
Just like Zorro!

If Jerry Maguire is to have continued success he is going to need to put in some serious hours to make things work. The problem with that is it will take him away from his new wife who just so happens to be the same wife he has already separated from once. It is hard to imagine that their second go at the relationship will stand any chance when Jerry is working away all of the time.

The bitter truth here is if Jerry Maguire manages any form of success as a sports agent his relationship with his wife will fail and if his work life fails to be successful a man like Jerry Maguire will probably put unnecessary pressure on his stepson to succeed in sports in some way. As the movie ended we already know that Jerry thinks the kid has a talent. Either way it is highly likely Jerry and his wife will be divorced within a year.

Toy Story 3


Toy Story 3 is the final instalment in the Toy Story trilogy. The movie follows everyone’s favourite toys as they struggle to find a new place to live since their owner Andy has grown up and left for college.

The Happy Ending

After narrowly avoiding an eternity in a landfill or hard time in the children’s day care centre Woody, Buzz and the other toys finally have the break they were all hoping for. Andy packs them all up into a box and gives them to a young girl he sees playing her garden.

The movie ends with us all assuming that they toys all live happily ever after with their new owner and avoid the landfill once and for all.

The Reality

It is a lovely thought to think that the little girl and new owner of the toys will look after them and play with them always but this simply is not going to happen.

While Buzz Lightyear and Woody were once some kids pride and joy new toys come along to replace them. Heck we even saw how Woody was nearly thrown away when the new Buzz Lightyear came alone. The harsh truth here is computers and electronic toys are quickly replacing most toys and the handed down toys will be lucky if they survive a week before the little girl is bored with them and they are send to live out their remaining days at the bottom of her toy chest. The only place from there is the landfill.

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